KR860000247A - Method for preparing 4-amino-butyrate derivative - Google Patents

Method for preparing 4-amino-butyrate derivative Download PDF

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KR860000247A
KR860000247A KR1019850003932A KR850003932A KR860000247A KR 860000247 A KR860000247 A KR 860000247A KR 1019850003932 A KR1019850003932 A KR 1019850003932A KR 850003932 A KR850003932 A KR 850003932A KR 860000247 A KR860000247 A KR 860000247A
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amino
butyric acid
acid derivative
derivative according
radical
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데깡 마르셀 (외 1)
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미쉘드 아스
사노피 소시에떼 아노님
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/02—Lithium compounds
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    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/04—Sodium compounds
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    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/06—Potassium compounds
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
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    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Abstract

The invention relates to 4-amino-butanoic acid derivatives of general formula: <IMAGE> in which: M represents an alkali metal atom, R represents a protected amino group, R1 represents a labile group, R2 represents hydrogen, a branched- or straight-chain alkyl radical having from 1 to 6 carbon atoms, a lower methyloxyalkyl, a lower methylthioalkyl, a lower (lower alkyl)-aminoalkyl, a lower di-(lower alkyl)-aminoalkyl or a lower hydroxyalkyl radical or R2 represents one of the radicals of general formulae: Cy-A-, Cy-O-A'-, R-A'- or R3S-A'- in which: Cy represents an aromatic or alicyclic hydrocarbon radical or heterocyclic radical having one oxygen or sulphur atom or one or two nitrogen atoms, Cy being optionally mono-, di- or tri-substituted by radicals comprising hydroxy, lower alkyl, lower alkoxy, trifluoromethyl, nitro or halogeno radicals, A represents a single bond or a branched- or straight-chain alkylene radical having from 1 to 5 carbon atoms, A' represents a branched- or straight-chain alkylene radical having from 1 to 5 carbon atoms, R3 represents a S-protecting group. These compounds are useful as intermediate products more particularly for the final synthesis of (3S,4S)-3-hydroxy-4-amino-6-methyl-heptanoic acid or statine.

Description

4-아미노-낙산유도체의 제조방법Method for preparing 4-amino-butyrate derivative

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (23)

다음 일반식 (Ⅰ)-(Ⅰ')의 4-아미노-낙산 유도체.4-Amino-butyric acid derivatives of the following general formulas (I)-(I ′). 제1항에 있어서, R2가 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸, tert-부틸, 1-메틸-프로필, n-펜틸 또는 n-헥실라메칼, 메톡시에틸, 메틸티오에틸, 메틸아미노에틸, 에틸아미노에틸, 이소프로필아미노에틸, tert-부틸아미노에틸, 디메틸아미노에틸, 디에틸아미노에틸, 디-n-프로필아미노에틸, 디-n-부틸아미노에틸, 히드록시메틸, 1-히드록시-에틸, 페닐, 히드록시페닐, 메틸페닐, 모노-플로오로-, 모노-클로로-또는 모노-브로모-페닐, 디-플루오로-, 디-클로로-또는 디-브로모-페닐, 모노-메톡시-, 디-메톡시-또는 트리-메톡시-페닐, 트리플루오로메틸페닐, 니트로페닐, 벤질, 페네틸, 사이클로헥실, 사이클로헥실메틸, 피콜릴, 피페리디노메틸, 인돌릴메틸, 1H-이미다졸릴메틸, 페녹시에틸, 페녹시-n-프로필, N-보로4-아미노-부틸 또는 s-보호 더캅토 메틸 라디칼을 나타내는 4-아미노-낙산 유도체.The compound of claim 1, wherein R 2 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 1-methyl-propyl, n-pentyl or n-hexylamecal, methoxyethyl , Methylthioethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, dimethylaminoethyl, diethylaminoethyl, di-n-propylaminoethyl, di-n-butylaminoethyl, hydride Hydroxymethyl, 1-hydroxy-ethyl, phenyl, hydroxyphenyl, methylphenyl, mono-fluoro-, mono-chloro- or mono-bromo-phenyl, di-fluoro-, di-chloro- or di-bro Parent-phenyl, mono-methoxy-, di-methoxy- or tri-methoxy-phenyl, trifluoromethylphenyl, nitrophenyl, benzyl, phenethyl, cyclohexyl, cyclohexylmethyl, picolyl, piperidinomethyl , Indolylmethyl, 1H-imidazolylmethyl, phenoxyethyl, phenoxy-n-propyl, N-boro4-amino-butyl or s-protected decaptomethyl 4-amino represents the radical - butyric acid derivative. 제1항 또는 2항에 있어서, R2가 메틸을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents methyl. 제1항 또는 제2항에 있어서, R2가 에틸을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents ethyl. 제1항 또는 2항에 있어서, R2가 n-프로필을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents n-propyl. 제1항 또는 2항에 있어서, R2가 이소프로필을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents isopropyl. 제1항 또는 2항에 있어서, R2가 n-부틸을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents n-butyl. 제1항 또는 2항에 있어서, R2가 이소부틸을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents isobutyl. 제1항 또는 2항에 있어서, R2가 1-메틸-프로필을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents 1-methyl-propyl. 제1항 또는 2항에 있어서, R2가 페닐을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents phenyl. 제1항 또는 2항에 있어서, R2가 벤질을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents benzyl. 제1항 또는 2항에 있어서, R2가 4-히드록시-페닐을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents 4-hydroxy-phenyl. 제1항 또는 2항에 있어서, R2가 사이클로 헥실을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents cyclohexyl. 제1항 또는 2항에 있어서, R2가 사이클로헥실메틸을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents cyclohexylmethyl. 제1항 또는 2항에 있어서, R2가 3-인돌릴-메틸을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents 3-indolyl-methyl. 제1항 또는 2항에 있어서, R2가 1H-이미다졸-4-일-메틸을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to claim 1 or 2, wherein R 2 represents 1H-imidazol-4-yl-methyl. 제1항에서 16항중 어느 하나에 있어서, R이 tert-부틸옥시카르보닐아미노 그룹을 나타내는 4-아미노-낙산유도체.The 4-amino-butyrate derivative according to any one of claims 1 to 16, wherein R represents a tert-butyloxycarbonylamino group. 제1항에서 16항중 어느 하나에 있어서, R1이 메틸, 에틸, n-부틸, 이소부틸, tert-부틸, 벤질 또는 크실릴을 나타내는 4-아미노-낙산유도체.The 4-amino-butyrate derivative according to any one of claims 1 to 16, wherein R 1 represents methyl, ethyl, n-butyl, isobutyl, tert-butyl, benzyl or xylyl. 제1항에서 16항중 어느 하나에 있어서, M이 나트륨을 나타내는 4-아미노-낙산유도체.The 4-amino-butyric acid derivative according to any one of claims 1 to 16, wherein M represents sodium. 다음 일반식 (Ⅳ)의 N-보호(4S)-3-옥소-4-아미노-낙산유도체의 에스테르를 20℃이하와 수성매질에서 수산화 알칼리금속과 반응시켜 생성된 염을 반응매질로부터 분리시키는 것을 특징으로 하는 4-아미노-낙산유도체의 제조방법.The separation of the resulting salt from the reaction medium by reacting an ester of the N-protective (4S) -3-oxo-4-amino-butyric acid derivative of formula (IV) with an alkali metal hydroxide at or below 20 ° C and in an aqueous medium A method for producing the 4-amino-butyric acid derivative. 제20항에 있어서, N-보호(4S)-3-옥소-4-아미노-낙산유도체는 다음 일반식 (Ⅱ)의 N-보호이미다졸리들를 실온과 에스테르에서 비양성자성 용매의 존재하에 다음 일반식(Ⅲ)의 말론산 모노에스테르의 마그네슘 에놀레이트와 반응시켜 착체를 생성하고 강산의 존재하에 가수분해 시켜 제조시키는 것을 특징으로 하는 방법.21. The N-protected (4S) -3-oxo-4-amino-butyric acid derivative according to claim 20, wherein the N-protected imidazolines of the general formula (II) are subjected to the following in the presence of an aprotic solvent at A method of producing a complex by reacting with magnesium enolate of malonic acid monoester of general formula (III) to produce a complex and hydrolyzing in the presence of a strong acid. 제20항 또는 21항에 있어서, N-보호(4S)-3-옥소-4-아미노-낙산유도체의 에스테르의 알칼리금속염을 수산화알칼리금속에 의해 생성하고 생성된 염을 분리하며 N-보호(4S)-3-옥소-4-아미노-낙산유도체를 강산으로 산성화하여 재생시킴으로써 순수하지 않은 형태로 얻은 해당 N-보호(4S)-3-옥소-4-아미노-낙산유도체의 에스테르를 정제하는데 4-아미노-낙산 유도체를 사용하는 것을 특징으로 하는 방법.22. An alkali metal salt of an ester of N-protected (4S) -3-oxo-4-amino-butyric derivative is produced by alkali metal hydroxide and the resulting salt is isolated and N-protected (4S). 4) Purification of esters of the corresponding N-protected (4S) -3-oxo-4-amino-butyric derivatives obtained in non-purified form by acidifying and regenerating) -3-oxo-4-amino-butyrate derivatives with strong acids. Using amino-butyrate derivatives. 제20항에서 22항중 어느 하나에 있어서, 상기-4-아미노-낙산 유도체를 환원시켜 N-보호(3S,4S,3R,4S)-3-히드록시-4-아미노-낙산 유도체를 부분입체 이성질체 형태로 제조하여 이어서 분리시킴으로써 N-보호3-히드록시-4-아미노낙산 유도체의 에스테르의 (3S,4S) 및 (3R,4S)부분 입체이성질체를 제조하는데 4-아미노-낙산유도체를 사용하는 것을 특징으로 하는 방법.23. The N-protective (3S, 4S, 3R, 4S) -3-hydroxy-4-amino-butyric derivative is prepared as a diastereomer according to any one of claims 20 to 22. The use of 4-amino-butyric derivatives to prepare (3S, 4S) and (3R, 4S) diastereomers of esters of N-protected 3-hydroxy-4-aminobutyric acid derivatives by preparing in the form and then separating them How to feature. 여기서, M은 리튬, 나트륨 또는 칼륨과 같은 알칼리금속 원자를 나타내고, R은 아미노 보호그룹을 나타내고, R1은 불안정한 그룹을 나타내고, R2는 수소, 또는 메틸, 에틸, n-프로필, 이소프로필 n-부틸, 이소부틸, tert-부틸, 1-메틸-프로필, n-펜틸 또는 n-헥실과 같은 1-6개의 탄소원자를 갖는 가지달린 또는 곧은 사슬 알칼라디칼, 또는 메틸옥시에틸과 같은 저급메틸옥시알킬 라디칼, 또는 메틸티오메틸과 같은 저급메틸티오알칼라디칼, 또는 메틸아미노-, 에틸아미노-, 이소프로필아미노-또는 tert-부틸아미노-에틸과 같은 저급(저급알킬)-아미노알킬 라디칼, 또는 디메틸아미노-, 디에틸아미노-, 더-n-프로필아미노-또는 디-n-부틸아미노-에틸과 같은 저급 디-(저급알킬)-아미노알킬 라디칼, 또는 히드록시메틸 또는 1-히드록시에틸과 같은 저급히드록시알킬 라디칼을 나타내고, R2는 다음 일반식의 라디칼 중 하나를 나타낸다. Cy-A-, Cy-O-A', R-A', R3S-A'-이때 Cy는 방향족 또는 지방족 고리 탄화수소라디칼, 또는 하나의 산소 또는 황원자 또는 1 또는 2개의 질소원자를 가지고 있는 헤테로고리라디칼을 나타내고 히드록시, 저급알킬, 저급알콕시, 트리플루오로메틸, 니트로-또는 할로게노-라디칼로 구성된 라디칼에 의해 선택적으로 모노-, 디-또는 트리-치환되며, A는 단일결합 또는 1-5개의 탄소원자를 갖는 가지달린 또는 곧은 사슬 알킬렌 라디칼을 나타내고, A'는 1-5개의 탄소원자를 갖는 가지달린 또는 곧은 사슬 알킬렌 라디칼을 나타내고, R3는 s-보호그룹을 나타낸다.Where M represents an alkali metal atom such as lithium, sodium or potassium, R represents an amino protecting group, R 1 represents an unstable group, R 2 represents hydrogen or methyl, ethyl, n-propyl, isopropyl n -Branched or straight chain alkalis having 1-6 carbon atoms, such as -butyl, isobutyl, tert-butyl, 1-methyl-propyl, n-pentyl or n-hexyl, or lower methyloxyalkyl such as methyloxyethyl Radicals, or lower methylthioalkalicals such as methylthiomethyl, or lower (lower alkyl) -aminoalkyl radicals such as methylamino-, ethylamino-, isopropylamino- or tert-butylamino-ethyl, or dimethylamino- , Lower di- (lower alkyl) -aminoalkyl radicals such as diethylamino-, the-n-propylamino- or di-n-butylamino-ethyl, or lower hydrides such as hydroxymethyl or 1-hydroxyethyl Oxyalkyl Represents the radical, R 2 represents one of the following: a radical of general formula. Cy-A-, Cy-O-A ', R-A', R 3 S-A'- wherein Cy is an aromatic or aliphatic ring hydrocarbon radical, or having one oxygen or sulfur atom or one or two nitrogen atoms Represents a heterocyclic radical and is optionally mono-, di- or tri-substituted by a radical consisting of hydroxy, lower alkyl, lower alkoxy, trifluoromethyl, nitro- or halogeno- radicals, A being a single bond or 1 -Represents a branched or straight chain alkylene radical having 5 carbon atoms, A 'represents a branched or straight chain alkylene radical having 1-5 carbon atoms, and R 3 represents an s-protecting group. ※ 참고사항 : 최초출원내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019850003932A 1984-06-06 1985-06-05 Method for preparing 4-amino-butyrate derivative KR860000247A (en)

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